Method of producing rapid drying



' Patented Aug. 7,1945

METHOD OF PRODUCING RAPID DRYING COATING COMPOSITIONS Folsom E. Drummond, Metuchen, N. J., asslgnor to New Wrinkle, Inc., Wilmington, Del., a corporation of Delaware No Drawing. Original appllcation'Api-il 10, 1939,

Serial No. 266,959, new Patent No. 2,268,022, dated December 30, 1941. Divided and this application September 24, 1941, Serial No.

9 Claims. (Cl. 106-264) This invention relates to method of producing rapid drying coating compositions, and is a division of my co-pending application Serial No. 266,959, filed April 10, 1939, which was granted December 30, 1941, as Patent No. 2,268,022.

More particularly my invention refers to method of producing rapid drying compositions (b) 'Irig lyceryl-isolinolenate CHa-(CH2)(CH==CH)sCH:-

of the drying oil and wrinkle finish type. The -Q invention, however, is applicable broadly in the CH3 (Cm)'(CH=CH)* CH production of protective and decorative coating CH=CH(CH2)7COO C compositions such as varnishes, paints, enamels, printing inks' and the like.

I have discovered that the drying of coating compositions can be controlled so as to produce either rapid drying smooth surface compositions or compositions drying to a wrinkle finish, the control being exercised by varying the amount of compounds present having conjugated double band structure of the general formula lit CH3(CH2) -(CH=CH) 2-0112-- 7 CH=CH(CH:) 1000-0-11: (0) 'Iriglyceryl-elaeostearate crh-hcinn-wnwmi-(cnin-coo-oni one-(cm) i-- cn=cm 3- wherein a: is equal to 2, 3 or 4. Examples of com- C0-(CHe)s-COOCH2 pounds'which comprise conjugated double bonds CI-Ia-(CI-Iz)a(CH=CH)a-(CHahare unsaturated acids such as the following: co-(crn)=-c0o o I-1 cm CHLC co cmn-coo-c-ni CH=CH(CH2) ICOOH I CO- (CH2) 2COOH Licanic acid CI-Ia-CHr-(CH=CH) 4-(CH2) qcoor-r Octadecatetraenoic acid These unsaturated fatty acid compounds are constituents of many fats, especially drying and semi-drying oils. In general, the higher the num-- ber of conJugated double bonds (CH=CH--) in the compound the more readily reactive it is. Similarly under the same conditions the greater the percentage amount of conjugated double bond compound in the coating him the shorter is the drying time. 7

In the formulation of rapid drying coating compositions or the drying 011 type. according to my invention, utilization is made principally of the tri-glycerides of the fatty acids having polyconjugated double bond molecular structure as heretofore mentioned.

Typical examples which illustrate the glycerides employed are: a

(a) Triglyceryl-isolinoleate (e) Trigylceryl-octadecatetraenate By incorporating various amounts of the triunsaturated zlycerides in the conventional nong paint oils the dryin Properties may be greatly enhanced and the waterproofing and flexibility oi the product increased. Further by compounding the paint oils with a sumcient amount of fatty acid triglyceride compounds haveride added varies with each oil but may comprise upwards of 50 percent by weight for producing wrinkling drying oil products. In this case the percentage amount of triglyceride is preferably in the neighborhood of per cent or I the paint oil composition.

produce the mostdi-unsaturated glycerides in Preferably the triglycerides are used since they place of the tri or mixtures thereof may be employed if desired. Further utilization may be made of the fatty acids alone when a sufiicient amount of glycerol or glyceride constituents is present in the oil mixture. The fatty acids alone in the absence of glycerol r glyceride compound do' not exhibit good drying properties.

Formulations made using the glycerides having only 2 conjugated double bonds produce a drying oil paint vehicle having superior drying. and waterproofing qualities to those of linseed oil. Addition of suitable metallic driers to these modified drying oil vehicles will further enhance the drying of the composition to a smooth nonwrinkling film when applied and air dried or baked at low temperatures.

Typical examples of non-wrinkling oil vehicles are as follows:

Example 1 v Per .cent by weight Linseed oil l to40 Triglyceryl-isolinoleate 85 to 80 Example 2 Linseed oil l5 to40 'I'riglyceryl-isolinolenate 85 to 60 Example 3 Perilla oil 1515040 Triglyceryl-isolinoleate 85 to 60 Example 4 Perilla oil l5 to40 Triglyceryl-isolinolenat 85 to 60 Example 5 bya bean o l to Triglyceryl-isolinoleate 90 to 70 Example 6 SOya bean oil 10 to 30 Triglyceryl-isolinolenate 90 to 70 Example 7 China-wood oil to 60 'lriglyceryl-isolinoleate 60 to 40 Example 8 China-wood oil 40 to 60 'lriglyceryl-isoiinolenate 80 to 40 In the examples of paint and varnish vehicles given the drying and semi-drying. oils may be used either in the raw state, refined Or in blown condition as desired. Various mixtures or the diii'erent oils also may be utilized. Furtheruse may be made or other oils, for example oiticica. poppy seed oil, sunflower oil, as well as fish and marine mammal oils heretofore used in paint and varnish coating compositions. i

The mixture of oil and glyceride is heated to incorporate the fatty acid glyceride to form a homogeneous composition. Heating the oil and glyceride mixture to a temperature 01850 to 450 degrees F. tor one half to one hour is suiiicisnt to produce a satisfactory product.

Suitable driers or drier combinations may be incorporated in the modified oil vehicles 11 desired, such as the acetate, resinate or linoleate of cobalt, manganese or lead.

The glyceride modified oil vehicles illustrated in Examples 1 to 8 may be compounded with suitable resins, naturslor synthetic; for example, kauri. conso, damar, pontianak, manila, elemi, mastic or synthetic resins such as Cumar," ester gum, phenol formaldehyde resin, glycerol-phthalic acid resin particularly of the oil soluble type or mixtures of these. The coating compositions employing the glyceride modified oil vehicles may be either air dried or baked to produce a dry, smooth, fiexible, water-resistant film. A baking temperature range between 250 to 400 degrees I". for one-half to one and one-half hours may be employed.

For the production of similar coating compcsitions wherein the film readily dries to a wrinkle finish surface, modified oil vehicles comprising large percentages of fatty acid glycerides having 3 or more conjugated double bond molecular structure are employed. 7

Typical examples of wrinkling all vehicles are:

Example 9 Percent by weight Linseed oil 5 to 25 Triglyceryl-elaeostearate 95 to '15 Example 10 Linseed oi .5 to 25 Triglyceryl-licanate 95 to Example 11 Linseed oil 20 to 40 Triglyceryl-octodecatetraenate to 60 Example 12 I Periila oil 5 to 25 'Iriglyceryl-olaeostearate ..l 95 to 75 Example 13 Perilla oil 5 to 25 Triglyceryl-licanate 95 to 75 Example 14 Periila nil 20 to 40 Triglyceryl-octodecatetraenate 80 to 60 Example 15 Soya been all 5 to 20 'Iriglyceryl-elaeostearate 95 to 80 I Example 16 Soya bean oil 5 to 20 Triglyceryl-licanate 95 to 80 Example 17 Soya bean oil 10 to 25 Triglyceryl-octodecatetraenate to 75,

In compounding the oil compositions of Exampl 9 to 17, the fatty acid glyeerides are thoroughly incorporated with the oils to provide a homogeneous drying oil vehicle in a similar manner to that described in Examples 1 to 8. It will be understood also that raw, refined or blown drying oils may be used in preparing the wrinkling oils. In general when using blown or prepolymerized oils less amount of the glyceride constituent is required to produce a product which will dry in a given time.

The glycerides having triple or more conjugated double bonds may also be blended with tung oil or oiticica, which are wrinkling oils, to modify their wrinkling characteristics. In like manner the incorporation of natural or synthetic resins and driersmay be made.

The compositions comprising the modified drying oil may be applied as a film by fiowing or spraying and baked at temperatures of the order of 250 to 350 degrees I". for one to two hours to produce a wrinkle finish. Enamels require somewhat longer and higher temperatures of baking. For thinning the paint oil vehicles, petroleum naphtha, toluol, or mixtures of the two may be employed. a

Further in utilizing the wrinkling 0118 Of E3 amples 9 to 17 the use of various natural or synthetic resins may be made to provide a resinous type coating composition. Various resins may be added to the composition in order to modify the properties comprising natural and synthetic resins such as heretofore mentioned. When it is desired to give added flexibility to the films, a suitable plasticizing agent'such as castor oil, dibutyl phthalate or tri-cresyl-phosphatemay be incorporated. The paint oil compositions herein illustrated can also be used in making enamels and similar pigmented compositions. To produce such compositions 5 to 25% of a suitable pigment is ground into the glyceride modified oil or resinous oil composition and the required amount of thinner such as'petroleum naphtha and the like is added.

Clear varnish-like compositions may be applied over various articles and baked either to a wrinkle finisher a smooth glossy surface depending upon whether the oils are those of Examples 1 to 8 or the wrinkling oils of Examples 9 to 1'1. Thin coatings may also be applied over materials such as paper, foil, parchment and the like to produce a light transmitting sheet applicable for making various articles such as window shades, drapes, lamp shades and the like. The coating compositions of this invention may also be applied over metal, wood, pottery, glass, paper, leather and the like, and baked or air dried to a flexible, tough film. Various ornamental effects of the wrinkle finishes can be produced by varying It will be understood that while 1 have described and illustrated certain specific embodiments of my invention, I do not intend that my a,ssi,oss

or like composition disposed formula (-CH==CH--):c, wherein a: is equal to a' value the lower limit of which is 2 and the upper limit 4; and heating said oil-trigly eride mixture to a temperature of from 850 to 450 1". for one-half to one hour.

3. The method of accelerating the rate of drying consisting of incorporating into drying oil a high molecular weight fatty acid glyceride of the class consisting of diglyceride and triglyceride, said fatty acid having 18 carbon atoms and a polyconiugated double bond structure of the formula (-CH=CH-'--):r,' wherein a: is equal to 2; and heating said oil-glyceride mixture to a temperature of from 350 to 450 F. for one-half to one hour.

4. The method of accelerating the rate of drying consisting of incorporating into drying oil a high molecular weight fatty acid glyceride of the class consisting of diglyceride and triglyceride.

5. The method of accelerating the rate of drying consisting of incorporating into drying oil a high molecular weight fatty acid glyceride of the class consisting of diglyceride and triglyceride,

said fatty acid having 18 carbon atoms and a polyconiugated double bond structure of the formula (--CH=CH)1:, wherein a: is equal to 4;

and heating said oil-glyceride mixture to a temperature of from 350 to 450 F. for one-half to one hour.

' 8. The method of accelerating the rate of dry-- ing consisting of incorporating into drying oil high molecular weight fatty acid triglycerides,

said fatty acid having 18 carbon atoms and a polyconiugated double bond structure of the formula (CH=CH-) 2:, wherein a: is equal to 2; and heating said oil-triglyceride mixture to a temperature of from 850 to 450 F. for one-half to one hour.

, 'i. The method of accelerating the rate of drying consistingof incorporating into drying oil invention be limitedto or circumscribed by the specific details of procedure andproportions indicated in view of the fact that the details of my invention may be varied and modified over a wide range within the spiritand scope of the appended-claims.

It will be further understood that the term "nonwrinklingdrying oils, as used in the claims,

is intended to encompass drying oils and semifor one-half to one hour.

2. The method of accelerating'the rate of drying consisting of incorporating into drying oil high molecular weight fatty acid triglycerides.

. said fatty acid having 18 carbon atoms and a' roiyconiugated double bond structure 0! the high molecular weight fatty acid triglycerides. said fatty acid havng 18 carbon atoms and a polyconiugated double bond structure of the formula (CH -CH) 1:, wherein :c is equal to 3: and heating said oil-triglyceride mixture to a temperature oi from 850' to 450 F. for one-half to one hour.

8. The method of accelerating the rats of dry in: consisting of incorporating into drying oil high molecular weight fatty acid triglycerides said fatty acid having18 carbon atoms and a polyeoniugated double bond structure of the formula (--CH==C'H-) 2:. wherein a is equal to 4;

and heating said oil-triglyceride mixture to a temperature of from 850 to 450' 1". for one-half to one hour.

glyceride and triglyceride, said fatty acid having 18 carbon atoms and a" nolyconiugated double bond structure of the formula (-CH=CH-) 1:,

wherein a: is equal to a value the lower limit of which is 2 and the upper limit 4; and heating said oil-glyccride .mixtureto a temperature of from 850 to soil 1". for one-halite one hour. I. DRUWOND. 

